The instant invention provides 3,7-dimethyl-6,7-dioxo-1,3-octadienes defined according to the generic structure: ##STR3## wherein R represents hydrogen or ethyl; wherein X represents one of the moieites: ##STR4## and wherein the wavy lines represent a "E" or "Z" configuration of the methyl and vinyl moiety about the 3,4 double bond of the molecule, as well as the uses thereof for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.
Inexpensive chemical compositions of matter which can provide intense and highly substantive herbaceous, cut geranium stem, floral, fresh fruity, natural green and leafy aromas with floral and citrusy topnotes and fruity, melony, peppery and citrusy undertones are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Indeed, marigold absolute has been found by us to contain very small quantities of the compounds having the structures: ##STR5## However, these components of marigold absolute have unexpected, unobvious and advantageous perfumery properties with respect to intensity and substantivity when compared with marigold absolute itself.
Arctander, "Perfume and Flavor Materials of Natural Origin", 1960, published by the author discloses at page 399:
Marigold Absolute. PA0 Also called Calendula absolute, Marigold Absolute is extracted from the ligulate florets of Calendula Officinalis, known as "Marigold", "Marybud" or "Hollygold" in the United States of America. There is, however, some confusion with respect to the term "marigold" since it has been applied to various other plants of the Compositae family, e.g. Tagetes, etc. Tagetes will be described under its proper name. PA0 The calendula absolute from the true calendula officinalis is probably produced only in France, but it is sold in English speaking countries under the name of Marigold. PA0 The absolute is a very dark greenish-brown, very viscous liquid of an intensely bitter-herbaceous odor. Little is known about its constituents, but as a perfumery material, it has certain interesting and unique notes. Since the plant grows commonly all over Europe, cultivated in the northern part, an increased production could easily be effected. PA0 Its very peculiar note and intense color, however, limits the use of "marigold" to fancy perfume types, modern aldehydic-herbaceous types where the green "crushed-stalk" note may be called for. Marigold Absolute introduces certain natural notes in chrysanthemum fragrances, and it gives interesting effects with oakmoss, mate extract, tea leaf extract, cypriol, iso cyclo citral, etc. Traces of the absolute can be useful in hyacinth, lilac, gardenia, reseda, moss-bases, etc. PA0 See also Tagetes, under which Tagetes Glandulifera is discussed, and Tagetes Patula under which heading the Indian "genda" is mentioned.
Tsankova and Bohlmann, "A Monoterpene From Aster Bakeranus", Phytochemistry, Volume 22, No. 5, pages 1285-1286, 1983 discloses that the compound having the structure: ##STR6## is present in the South African species, Aster bakeranus Burtt, Davy ex. C. A. Smith.
Merchant, et al, Indian J. Chem., Volume 14B, Jun. 1976, at pages 460 and 461 discloses the saturated ether derivative having the structure: ##STR7## and the synthesis thereof.
Nothing in the prior art, however, discloses the organoleptic properties and particularly the perfume utilities of the 3,7-dimethyl-6,7-dioxo-1,3-octadienes of our invention; and, indeed, nothing in the prior art discloses the compound having the structure: ##STR8## wherein X is one of the moieties: ##STR9## and wherein the wavy lines represent the "E" or "Z" configuration of the vinyl and methyl moiety about the 3,4-pi-bond.